Diisopropylethylamine → ethyl 5-(2-(dimethylamino)-[1,2,4]triazolo[1,5-a]pyridin-7-ylcarbamoyl)-1-methyl-1H-pyrazole-4-carboxylate

HRID 1802205Notes

Reaction equation

HRID 1802205 reaction equation
[CH3:1][N:2]([CH3:13])[C:3]1[N:12]=[C:6]2[CH:7]=[C:8]([NH2:11])[CH:9]=[CH:10][N:5]2[N:4]=1.[CH2:14]([O:16][C:17]([C:19]1[CH:20]=[N:21][N:22]([CH3:27])[C:23]=1[C:24](O)=[O:25])=[O:18])[CH3:15].CCCP(=O)=O.C(N(C(C)C)CC)(C)C>O1CCCC1>[CH3:1][N:2]([CH3:13])[C:3]1[N:12]=[C:6]2[CH:7]=[C:8]([NH:11][C:24]([C:23]3[N:22]([CH3:27])[N:21]=[CH:20][C:19]=3[C:17]([O:16][CH2:14][CH3:15])=[O:18])=[O:25])[CH:9]=[CH:10][N:5]2[N:4]=1

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 16167369Propylphosphoric anhydrideHCID 252475674-(Ethoxycarbonyl)-1-methyl-1H-pyrazole-5-carboxylic acidHCID 67774846N2,N2-dimethyl-[1,2,4]triazolo[1,5-a]pyridine-2,7-diamine

Product 1

HCID 67774271ethyl 5-(2-(dimethylamino)-[1,2,4]triazolo[1,5-a]pyridin-7-ylcarbamoyl)-1-methyl-1H-pyrazole-4-carboxylateYield 89.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of N2,N2-dimethyl-[1,2,4]triazolo[1,5-a]pyridine-2,7-diamine (700 mg, 3.95 mmol), 4-(ethoxycarbonyl)-1-methyl-1H-pyrazole-5-carboxylic acid (812 mg, 4.1 mmol), propylphosphonic anhydride (50% in ethyl acetate, 5.82 ml, 9.88 mmol) and diisopropylethylamine (2.07 ml, 11.9 mmol) in tetrahydrofurane (40 ml) is refluxed for 18 hours under nitrogen atmosphere. The solvent is evaporated and the residue triturated with sat. aqueous sodium hydrogencarbonate solution. The solid is collected by filtration, washed with water and dried affording ethyl 5-(2-(dimethylamino)-[1,2,4]triazolo[1,5-a]pyridin-7-ylcarbamoyl)-1-methyl-1H-pyrazole-4-carboxylate (1.26 g, 89.3%) as a light brown solid. Mp.: 193-5° C. MS: m/z=358.4 (M+H+).

Workup

  1. temperatureis refluxed for 18 hours under nitrogen atmosphere
  2. customThe solvent is evaporated
  3. customthe residue triturated with sat. aqueous sodium hydrogencarbonate solution
  4. filtrationThe solid is collected by filtration
  5. washwashed with water
  6. customdried

Sources & evidence

ORD record
ord-60bb7fab0f7f4748ab48af2a2db9743e
Source dataset
uspto-grants-2013_01
Patent number
US08349824B2

Reaction notes

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